PL88714B1 - 3-halo cephalosporins[au6591574a] - Google Patents
3-halo cephalosporins[au6591574a] Download PDFInfo
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- PL88714B1 PL88714B1 PL1974169033A PL16903374A PL88714B1 PL 88714 B1 PL88714 B1 PL 88714B1 PL 1974169033 A PL1974169033 A PL 1974169033A PL 16903374 A PL16903374 A PL 16903374A PL 88714 B1 PL88714 B1 PL 88714B1
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- Poland
- Prior art keywords
- ester
- thienyl
- carboxylic acid
- formula
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- Prior art date
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- -1 -halo cephalosporins Chemical class 0.000 title claims abstract description 279
- 229930186147 Cephalosporin Natural products 0.000 title description 6
- 229940124587 cephalosporin Drugs 0.000 title description 6
- 239000002253 acid Substances 0.000 claims abstract description 120
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 40
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims abstract description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 230000002140 halogenating effect Effects 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000006331 halo benzoyl group Chemical group 0.000 claims abstract description 3
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims abstract description 3
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 3
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims abstract 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims description 103
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 44
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052794 bromium Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000012320 chlorinating reagent Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 claims description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical group CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 6
- UUPZTFTUZUQRQT-UHFFFAOYSA-N 2-thiophen-2-ylacetamide Chemical group NC(=O)CC1=CC=CS1 UUPZTFTUZUQRQT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- MJSLXMHHSSCUOK-LRTDYKAYSA-N (4-nitrophenyl)methyl (6r)-3-chloro-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=C(Cl)CS[C@H]2N1C(=O)C2NC(=O)CC1=CC=CS1 MJSLXMHHSSCUOK-LRTDYKAYSA-N 0.000 claims 2
- YTCUEIOOUOMPAT-RXMQYKEDSA-N (6r)-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(O)CS[C@@H]2CC(=O)N12 YTCUEIOOUOMPAT-RXMQYKEDSA-N 0.000 claims 2
- ZLCROHOIGCYDHA-LRTDYKAYSA-N (4-nitrophenyl)methyl (6r)-3-bromo-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=C(Br)CS[C@H]2N1C(=O)C2NC(=O)CC1=CC=CS1 ZLCROHOIGCYDHA-LRTDYKAYSA-N 0.000 claims 1
- ZOLCBEAPQMPJLZ-ZZNDMADYSA-N (6R)-3-chloro-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C([C@H](O)C1=CC=CC=C1)(=O)NC1[C@@H]2N(C(=C(CS2)Cl)C(=O)O)C1=O ZOLCBEAPQMPJLZ-ZZNDMADYSA-N 0.000 claims 1
- JOPWATABERKASH-FFFFSGIJSA-N (6r)-3-chloro-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SCC(Cl)=C(N2C1=O)C(=O)O)NC(=O)CC1=CC=CS1 JOPWATABERKASH-FFFFSGIJSA-N 0.000 claims 1
- 101150026868 CHS1 gene Proteins 0.000 claims 1
- 229920006706 PC-C Polymers 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003457 sulfones Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 61
- 239000000203 mixture Substances 0.000 abstract description 54
- 150000007513 acids Chemical class 0.000 abstract description 21
- 125000004185 ester group Chemical group 0.000 abstract description 11
- 239000007858 starting material Substances 0.000 abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 9
- 231100000252 nontoxic Toxicity 0.000 abstract description 7
- 230000003000 nontoxic effect Effects 0.000 abstract description 7
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract description 4
- 230000006181 N-acylation Effects 0.000 abstract description 2
- YYSCKUIUUOYNNB-NQPNHJOESA-N (6R)-7-amino-3-methylidene-5-thia-1-azabicyclo[4.2.0]octan-8-one Chemical class C=C1CS[C@H]2N(C1)C(C2N)=O YYSCKUIUUOYNNB-NQPNHJOESA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001782 cephems Chemical class 0.000 abstract 1
- 230000006196 deacetylation Effects 0.000 abstract 1
- 238000003381 deacetylation reaction Methods 0.000 abstract 1
- 238000005947 deacylation reaction Methods 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 115
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- 150000001408 amides Chemical class 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 230000009102 absorption Effects 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 19
- 238000002329 infrared spectrum Methods 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 16
- 238000000921 elemental analysis Methods 0.000 description 15
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 101150041968 CDC13 gene Proteins 0.000 description 13
- 230000003115 biocidal effect Effects 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 230000010933 acylation Effects 0.000 description 11
- 238000005917 acylation reaction Methods 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 238000003776 cleavage reaction Methods 0.000 description 11
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000002211 ultraviolet spectrum Methods 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 230000002401 inhibitory effect Effects 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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- 230000007017 scission Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- 238000001228 spectrum Methods 0.000 description 7
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 241000191940 Staphylococcus Species 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
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- 238000003786 synthesis reaction Methods 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- 238000005949 ozonolysis reaction Methods 0.000 description 5
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
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- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 4
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- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33541473A | 1973-02-23 | 1973-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL88714B1 true PL88714B1 (en) | 1976-09-30 |
Family
ID=23311677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974169033A PL88714B1 (en) | 1973-02-23 | 1974-02-23 | 3-halo cephalosporins[au6591574a] |
Country Status (34)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT342197B (de) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | Neues verfahren zur herstellung von 3-cephemverbindungen |
| CH622802A5 (enrdf_load_html_response) * | 1975-08-20 | 1981-04-30 | Ciba Geigy Ag | |
| IE45158B1 (en) * | 1976-08-16 | 1982-06-30 | Lilly Co Eli | 3-chloro-cephem synthesis |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| JPS62112053U (enrdf_load_html_response) * | 1985-12-27 | 1987-07-16 | ||
| IT1255458B (it) * | 1992-05-11 | 1995-11-02 | Col Marco Da | Procedimento per la preparazione di derivati beta-lattamici alogenati |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2265798C2 (de) * | 1971-06-24 | 1985-09-26 | Fujisawa Pharmaceutical Co., Ltd., Osaka | Verfahren zur Herstellung von Oxoazetidin-Derivaten |
-
1974
- 1974-01-01 AR AR256545A patent/AR208068A1/es active
- 1974-02-21 AT AT142474A patent/AT333952B/de not_active IP Right Cessation
- 1974-02-22 GT GT197432132A patent/GT197432132A/es unknown
- 1974-02-22 NO NO740607A patent/NO148376C/no unknown
- 1974-02-22 ZM ZM36/74A patent/ZM3674A1/xx unknown
- 1974-02-22 YU YU0463/74A patent/YU36971B/xx unknown
- 1974-02-22 MW MW5/74*UA patent/MW574A1/xx unknown
- 1974-02-22 ES ES423532A patent/ES423532A1/es not_active Expired
- 1974-02-22 HU HUEI527A patent/HU167749B/hu unknown
- 1974-02-22 CY CY1042A patent/CY1042A/xx unknown
- 1974-02-22 FI FI526/74A patent/FI63240C/fi active
- 1974-02-22 AR AR252494A patent/AR200908A1/es active
- 1974-02-22 DE DE2408686A patent/DE2408686C2/de not_active Expired
- 1974-02-22 GB GB809674A patent/GB1458293A/en not_active Expired
- 1974-02-22 FR FR7406154A patent/FR2218878B1/fr not_active Expired
- 1974-02-22 IE IE00357/74A patent/IE38916B1/xx unknown
- 1974-02-22 BR BR1385/74A patent/BR7401385D0/pt unknown
- 1974-02-22 IL IL44263A patent/IL44263A/en unknown
- 1974-02-22 NL NLAANVRAGE7402486,A patent/NL181010C/xx not_active IP Right Cessation
- 1974-02-22 CA CA193,238A patent/CA1032532A/en not_active Expired
- 1974-02-22 BE BE1005740A patent/BE811494A/xx not_active IP Right Cessation
- 1974-02-22 ZA ZA00741190A patent/ZA741190B/xx unknown
- 1974-02-22 DD DD176752A patent/DD110277A5/xx unknown
- 1974-02-22 SE SE7402414A patent/SE411211B/xx not_active IP Right Cessation
- 1974-02-22 BG BG025871A patent/BG22404A3/xx unknown
- 1974-02-23 JP JP49021871A patent/JPS612677B2/ja not_active Expired
- 1974-02-23 RO RO7477795A patent/RO64595A/ro unknown
- 1974-02-23 PL PL1974169033A patent/PL88714B1/pl unknown
- 1974-02-23 OA OA55127A patent/OA04688A/xx unknown
- 1974-02-25 CS CS741377A patent/CS189625B2/cs unknown
- 1974-02-25 CH CH265474A patent/CH594686A5/xx not_active IP Right Cessation
- 1974-11-15 AR AR256546A patent/AR201709A1/es active
-
1977
- 1977-02-11 PH PH19444A patent/PH14014A/en unknown
-
1979
- 1979-08-10 NO NO792609A patent/NO792609L/no unknown
-
1980
- 1980-02-27 KE KE3026A patent/KE3026A/xx unknown
- 1980-04-11 YU YU0998/80A patent/YU37347B/xx unknown
- 1980-04-17 HK HK199/80A patent/HK19980A/xx unknown
-
1981
- 1981-02-20 JP JP2533181A patent/JPS56138193A/ja active Granted
- 1981-02-20 JP JP2533381A patent/JPS56138195A/ja active Granted
- 1981-02-20 JP JP2533281A patent/JPS56138194A/ja active Granted
- 1981-12-30 MY MY23/81A patent/MY8100023A/xx unknown
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